NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	244.16
Volume:	268.485
LogP:	3.892
LogD:	3.921
LogS:	-3.487
# Rotatable Bonds:	5
TPSA:	45.75
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.873
Synthetic Accessibility Score:	2.646
Fsp3:	0.467
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.692
MDCK Permeability:	2.4673838197486475e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.571
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.105
30% Bioavailability (F30%):	0.087

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.425
Plasma Protein Binding (PPB):	96.43438720703125%
Volume Distribution (VD):	1.303
Pgp-substrate:	1.2942135334014893%

ADMET: Metabolism

CYP1A2-inhibitor:	0.961
CYP1A2-substrate:	0.939
CYP2C19-inhibitor:	0.887
CYP2C19-substrate:	0.355
CYP2C9-inhibitor:	0.815
CYP2C9-substrate:	0.236
CYP2D6-inhibitor:	0.383
CYP2D6-substrate:	0.133
CYP3A4-inhibitor:	0.625
CYP3A4-substrate:	0.488

ADMET: Excretion

Clearance (CL):	3.415
Half-life (T1/2):	0.317

ADMET: Toxicity

hERG Blockers:	0.119
Human Hepatotoxicity (H-HT):	0.158
Drug-inuced Liver Injury (DILI):	0.775
AMES Toxicity:	0.076
Rat Oral Acute Toxicity:	0.452
Maximum Recommended Daily Dose:	0.758
Skin Sensitization:	0.128
Carcinogencity:	0.377
Eye Corrosion:	0.008
Eye Irritation:	0.596
Respiratory Toxicity:	0.928

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC105758

Natural Product ID:	NPC105758
*Common Name:**	2-[(3R)-Heptan-3-Yl]-1H-Quinazolin-4-One
IUPAC Name:	2-[(3R)-heptan-3-yl]-1H-quinazolin-4-one
Synonyms:
Standard InCHIKey:	DAQXBHJQHGIETF-LLVKDONJSA-N
Standard InCHI:	InChI=1S/C15H20N2O/c1-3-5-8-11(4-2)14-16-13-10-7-6-9-12(13)15(18)17-14/h6-7,9-11H,3-5,8H2,1-2H3,(H,16,17,18)/t11-/m1/s1
SMILES:	CCCC[C@@H](CC)c1nc2ccccc2c(n1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1797816
PubChem CID:	49801533
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0004788] Diazanaphthalenes [CHEMONTID:0004789] Benzodiazines [CHEMONTID:0000485] Quinazolines

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO1520	Callyspongia pseudoreticulata	Species	Callyspongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12828480]
NPO24252	Uvaria hamiltonii	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14552774]
NPO33632	Bacillus cereus 041381	Species	n.a.	n.a.	isolated from the Coastal mud	Baimajin, Danzhou, Hainan province of China	n.a.	PMID[21612927]
NPO24252	Uvaria hamiltonii	Species	Annonaceae	Eukaryota	leaf and stem	n.a.	n.a.	PMID[9584399]
NPO24252	Uvaria hamiltonii	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28694	Sanguisorba tenuifolia	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23819	Baccharis peruviana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1520	Callyspongia pseudoreticulata	Species	Callyspongiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23277	Lobophora papenfussii	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24585	Ocotea macropoda	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	2500.0	nM	PMID[533528]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC105758 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	590
0.1-0.2	7290
0.2-0.3	10504
0.3-0.4	15830
0.4-0.5	5192
0.5-0.6	2592
0.6-0.7	636
0.7-0.8	50
0.8-0.85	3
0.85-0.9	1
0.9-0.95	5
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476688
1.0	High Similarity	NPC476686
0.987	High Similarity	NPC278874
0.9557	High Similarity	NPC208060
0.9484	High Similarity	NPC224632
0.9207	High Similarity	NPC477891
0.9207	High Similarity	NPC144114
0.9187	High Similarity	NPC164664
0.8772	High Similarity	NPC230805
0.8286	Intermediate Similarity	NPC254762
0.8239	Intermediate Similarity	NPC472289
0.805	Intermediate Similarity	NPC60553
0.7515	Intermediate Similarity	NPC26872
0.7457	Intermediate Similarity	NPC47298
0.7457	Intermediate Similarity	NPC315214
0.743	Intermediate Similarity	NPC283152
0.7414	Intermediate Similarity	NPC159319
0.7414	Intermediate Similarity	NPC32028
0.7386	Intermediate Similarity	NPC44161
0.7374	Intermediate Similarity	NPC288943
0.7333	Intermediate Similarity	NPC245657
0.7321	Intermediate Similarity	NPC161292
0.7283	Intermediate Similarity	NPC26850
0.7273	Intermediate Similarity	NPC280853
0.7255	Intermediate Similarity	NPC130570
0.7235	Intermediate Similarity	NPC288445
0.7229	Intermediate Similarity	NPC285016
0.7216	Intermediate Similarity	NPC97367
0.7212	Intermediate Similarity	NPC471596
0.7167	Intermediate Similarity	NPC471294
0.7167	Intermediate Similarity	NPC259545
0.7159	Intermediate Similarity	NPC177404
0.7151	Intermediate Similarity	NPC126481
0.7151	Intermediate Similarity	NPC153769
0.7143	Intermediate Similarity	NPC84508
0.7135	Intermediate Similarity	NPC62069
0.7104	Intermediate Similarity	NPC72980
0.7101	Intermediate Similarity	NPC471598
0.71	Intermediate Similarity	NPC471603
0.7097	Intermediate Similarity	NPC42591
0.7079	Intermediate Similarity	NPC62995
0.7072	Intermediate Similarity	NPC474409
0.7056	Intermediate Similarity	NPC473764
0.7056	Intermediate Similarity	NPC314940
0.7033	Intermediate Similarity	NPC303225
0.7021	Intermediate Similarity	NPC66083
0.7011	Intermediate Similarity	NPC232340
0.7006	Intermediate Similarity	NPC471594
0.6976	Remote Similarity	NPC48317
0.6968	Remote Similarity	NPC314573
0.6966	Remote Similarity	NPC59779
0.6966	Remote Similarity	NPC124542
0.6966	Remote Similarity	NPC471177
0.6952	Remote Similarity	NPC190007
0.6938	Remote Similarity	NPC2497
0.6927	Remote Similarity	NPC118511
0.6927	Remote Similarity	NPC473057
0.6915	Remote Similarity	NPC94943
0.6898	Remote Similarity	NPC212535
0.6898	Remote Similarity	NPC133306
0.689	Remote Similarity	NPC476689
0.689	Remote Similarity	NPC476685
0.689	Remote Similarity	NPC476687
0.6889	Remote Similarity	NPC471178
0.6882	Remote Similarity	NPC478032
0.6878	Remote Similarity	NPC472067
0.6878	Remote Similarity	NPC472031
0.6878	Remote Similarity	NPC472066
0.6878	Remote Similarity	NPC194040
0.6856	Remote Similarity	NPC242209
0.6836	Remote Similarity	NPC141353
0.6828	Remote Similarity	NPC88363
0.6821	Remote Similarity	NPC474188
0.6818	Remote Similarity	NPC36168
0.6816	Remote Similarity	NPC25899
0.6815	Remote Similarity	NPC81561
0.6777	Remote Similarity	NPC132631
0.6777	Remote Similarity	NPC103687
0.6772	Remote Similarity	NPC320394
0.6769	Remote Similarity	NPC472193
0.6757	Remote Similarity	NPC312872
0.6752	Remote Similarity	NPC148140
0.6744	Remote Similarity	NPC470404
0.6744	Remote Similarity	NPC470403
0.6744	Remote Similarity	NPC470394
0.6742	Remote Similarity	NPC477889
0.6739	Remote Similarity	NPC158129
0.6739	Remote Similarity	NPC252590
0.6731	Remote Similarity	NPC250178
0.6722	Remote Similarity	NPC131718
0.6722	Remote Similarity	NPC322644
0.672	Remote Similarity	NPC203754
0.672	Remote Similarity	NPC150048
0.6719	Remote Similarity	NPC183805
0.6717	Remote Similarity	NPC249040
0.6707	Remote Similarity	NPC278451
0.6702	Remote Similarity	NPC168486
0.6702	Remote Similarity	NPC171171
0.6702	Remote Similarity	NPC222592
0.6686	Remote Similarity	NPC114209
0.6685	Remote Similarity	NPC48192
0.6684	Remote Similarity	NPC96890
0.6684	Remote Similarity	NPC144381
0.6684	Remote Similarity	NPC204717
0.6667	Remote Similarity	NPC279401
0.6667	Remote Similarity	NPC470395
0.6667	Remote Similarity	NPC329541
0.6667	Remote Similarity	NPC248627
0.6667	Remote Similarity	NPC46580
0.6667	Remote Similarity	NPC79293
0.665	Remote Similarity	NPC208751
0.6649	Remote Similarity	NPC314002
0.6648	Remote Similarity	NPC314440
0.6648	Remote Similarity	NPC118135
0.6632	Remote Similarity	NPC128751
0.6632	Remote Similarity	NPC220765
0.6632	Remote Similarity	NPC246700
0.663	Remote Similarity	NPC120798
0.6615	Remote Similarity	NPC204385
0.6615	Remote Similarity	NPC324149
0.6607	Remote Similarity	NPC184437
0.6606	Remote Similarity	NPC39092
0.6601	Remote Similarity	NPC243850
0.6598	Remote Similarity	NPC469497
0.6598	Remote Similarity	NPC106833
0.6596	Remote Similarity	NPC184964
0.6593	Remote Similarity	NPC79911
0.6592	Remote Similarity	NPC120070
0.6591	Remote Similarity	NPC257142
0.6584	Remote Similarity	NPC215519
0.6582	Remote Similarity	NPC230403
0.6582	Remote Similarity	NPC45850
0.6578	Remote Similarity	NPC317054
0.6576	Remote Similarity	NPC108469
0.6569	Remote Similarity	NPC477111
0.6566	Remote Similarity	NPC70956
0.6566	Remote Similarity	NPC226662
0.6566	Remote Similarity	NPC153042
0.6566	Remote Similarity	NPC243834
0.6562	Remote Similarity	NPC162689
0.6562	Remote Similarity	NPC472068
0.6562	Remote Similarity	NPC54102
0.6557	Remote Similarity	NPC102423
0.6557	Remote Similarity	NPC476118
0.6553	Remote Similarity	NPC242923
0.6545	Remote Similarity	NPC243058
0.6545	Remote Similarity	NPC30540
0.6543	Remote Similarity	NPC134586
0.6533	Remote Similarity	NPC306376
0.6532	Remote Similarity	NPC295452
0.6532	Remote Similarity	NPC171393
0.6531	Remote Similarity	NPC99666
0.6526	Remote Similarity	NPC249662
0.6524	Remote Similarity	NPC313791
0.6514	Remote Similarity	NPC242556
0.651	Remote Similarity	NPC84478
0.651	Remote Similarity	NPC203635
0.6508	Remote Similarity	NPC219848
0.6508	Remote Similarity	NPC211997
0.6502	Remote Similarity	NPC475070
0.65	Remote Similarity	NPC476167
0.65	Remote Similarity	NPC280714
0.6492	Remote Similarity	NPC314394
0.6488	Remote Similarity	NPC18348
0.6488	Remote Similarity	NPC475910
0.6488	Remote Similarity	NPC470931
0.648	Remote Similarity	NPC284348
0.6477	Remote Similarity	NPC476319
0.6477	Remote Similarity	NPC476341
0.6474	Remote Similarity	NPC256268
0.6471	Remote Similarity	NPC477113
0.6471	Remote Similarity	NPC475841
0.6471	Remote Similarity	NPC474145
0.6468	Remote Similarity	NPC329747
0.6465	Remote Similarity	NPC276517
0.6465	Remote Similarity	NPC280638
0.6461	Remote Similarity	NPC37548
0.6458	Remote Similarity	NPC48938
0.6453	Remote Similarity	NPC53144
0.6453	Remote Similarity	NPC223427
0.6453	Remote Similarity	NPC200836
0.6452	Remote Similarity	NPC116622
0.6452	Remote Similarity	NPC317430
0.645	Remote Similarity	NPC192315
0.6447	Remote Similarity	NPC280964
0.6447	Remote Similarity	NPC114335
0.6447	Remote Similarity	NPC141915
0.6443	Remote Similarity	NPC90415
0.6443	Remote Similarity	NPC61350
0.6439	Remote Similarity	NPC53344
0.6436	Remote Similarity	NPC34508
0.6435	Remote Similarity	NPC187145
0.6429	Remote Similarity	NPC183407
0.6429	Remote Similarity	NPC129721
0.6429	Remote Similarity	NPC330009
0.6425	Remote Similarity	NPC309845
0.6425	Remote Similarity	NPC285923
0.6424	Remote Similarity	NPC122718
0.6422	Remote Similarity	NPC264166
0.6422	Remote Similarity	NPC165349

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC105758 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	356
0.1-0.2	799
0.2-0.3	649
0.3-0.4	1794
0.4-0.5	2675
0.5-0.6	2149
0.6-0.7	674
0.7-0.8	49
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8772	High Similarity	NPD9714	Clinical (unspecified phase)
0.8589	High Similarity	NPD444	Approved
0.809	Intermediate Similarity	NPD2410	Phase 2
0.7967	Intermediate Similarity	NPD6594	Discontinued
0.7923	Intermediate Similarity	NPD4673	Phase 2
0.788	Intermediate Similarity	NPD7419	Discontinued
0.7826	Intermediate Similarity	NPD3261	Phase 1
0.776	Intermediate Similarity	NPD5428	Discontinued
0.7657	Intermediate Similarity	NPD3224	Phase 2
0.765	Intermediate Similarity	NPD4401	Phase 2
0.765	Intermediate Similarity	NPD4403	Phase 3
0.7568	Intermediate Similarity	NPD3403	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1043	Phase 3
0.7474	Intermediate Similarity	NPD6307	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD1684	Approved
0.7457	Intermediate Similarity	NPD1685	Approved
0.7456	Intermediate Similarity	NPD2882	Phase 1
0.7435	Intermediate Similarity	NPD6132	Phase 1
0.7423	Intermediate Similarity	NPD852	Discontinued
0.7414	Intermediate Similarity	NPD5925	Phase 1
0.7376	Intermediate Similarity	NPD1954	Phase 1
0.7368	Intermediate Similarity	NPD3814	Phase 1
0.7353	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD6158	Phase 2
0.732	Intermediate Similarity	NPD6403	Clinical (unspecified phase)
0.7291	Intermediate Similarity	NPD3234	Phase 3
0.7291	Intermediate Similarity	NPD3233	Phase 2
0.7282	Intermediate Similarity	NPD1197	Approved
0.7273	Intermediate Similarity	NPD2794	Discontinued
0.7267	Intermediate Similarity	NPD9187	Approved
0.7238	Intermediate Similarity	NPD6159	Phase 2
0.7234	Intermediate Similarity	NPD4615	Phase 2
0.7225	Intermediate Similarity	NPD5885	Approved
0.7211	Intermediate Similarity	NPD7935	Phase 2
0.7198	Intermediate Similarity	NPD1503	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD639	Discontinued
0.7174	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD983	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD5529	Phase 1
0.7157	Intermediate Similarity	NPD5528	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD2524	Discontinued
0.715	Intermediate Similarity	NPD1838	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD6490	Phase 2
0.7143	Intermediate Similarity	NPD6887	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD3439	Approved
0.7101	Intermediate Similarity	NPD1273	Discontinued
0.7097	Intermediate Similarity	NPD2762	Phase 2
0.709	Intermediate Similarity	NPD6022	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD1313	Approved
0.7079	Intermediate Similarity	NPD7112	Discontinued
0.7079	Intermediate Similarity	NPD926	Approved
0.7079	Intermediate Similarity	NPD925	Approved
0.7068	Intermediate Similarity	NPD1912	Approved
0.7067	Intermediate Similarity	NPD6327	Phase 1
0.7067	Intermediate Similarity	NPD6326	Phase 2
0.7059	Intermediate Similarity	NPD2591	Phase 2
0.7053	Intermediate Similarity	NPD1234	Discontinued
0.7053	Intermediate Similarity	NPD2127	Suspended
0.7039	Intermediate Similarity	NPD4213	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD1215	Discontinued
0.703	Intermediate Similarity	NPD4358	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD4203	Approved
0.7027	Intermediate Similarity	NPD4204	Approved
0.7026	Intermediate Similarity	NPD6145	Phase 1
0.7021	Intermediate Similarity	NPD2383	Phase 1
0.7006	Intermediate Similarity	NPD6074	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3014	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3013	Phase 3
0.6995	Remote Similarity	NPD6958	Approved
0.6995	Remote Similarity	NPD3830	Phase 1
0.6995	Remote Similarity	NPD6957	Approved
0.6983	Remote Similarity	NPD509	Phase 3
0.6979	Remote Similarity	NPD4998	Phase 3
0.6979	Remote Similarity	NPD3810	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD4999	Phase 3
0.6978	Remote Similarity	NPD5996	Clinical (unspecified phase)
0.6976	Remote Similarity	NPD4312	Approved
0.6968	Remote Similarity	NPD7757	Approved
0.6968	Remote Similarity	NPD7758	Approved
0.6961	Remote Similarity	NPD7423	Phase 2
0.6957	Remote Similarity	NPD4945	Discontinued
0.695	Remote Similarity	NPD7409	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD2757	Phase 2
0.694	Remote Similarity	NPD9690	Approved
0.6927	Remote Similarity	NPD5176	Approved
0.6927	Remote Similarity	NPD38	Approved
0.6912	Remote Similarity	NPD6711	Approved
0.6904	Remote Similarity	NPD3765	Approved
0.6898	Remote Similarity	NPD5905	Phase 1
0.6892	Remote Similarity	NPD6724	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD6491	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD1599	Approved
0.6882	Remote Similarity	NPD2599	Approved
0.6882	Remote Similarity	NPD2600	Approved
0.6882	Remote Similarity	NPD2601	Approved
0.6882	Remote Similarity	NPD1592	Phase 3
0.6882	Remote Similarity	NPD702	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD3315	Phase 3
0.6875	Remote Similarity	NPD4950	Approved
0.6872	Remote Similarity	NPD3084	Phase 3
0.6865	Remote Similarity	NPD1272	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD7188	Phase 3
0.6862	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.686	Remote Similarity	NPD5070	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD3262	Approved
0.6853	Remote Similarity	NPD4511	Phase 1
0.6852	Remote Similarity	NPD6605	Phase 3
0.6851	Remote Similarity	NPD6794	Approved
0.6851	Remote Similarity	NPD425	Approved
0.6851	Remote Similarity	NPD424	Approved
0.6848	Remote Similarity	NPD3799	Suspended
0.6848	Remote Similarity	NPD6492	Phase 2
0.6847	Remote Similarity	NPD3976	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD3525	Discontinued
0.6834	Remote Similarity	NPD3500	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD404	Discontinued
0.6831	Remote Similarity	NPD2993	Clinical (unspecified phase)
0.683	Remote Similarity	NPD4438	Approved
0.6825	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD3931	Approved
0.6818	Remote Similarity	NPD3928	Approved
0.6816	Remote Similarity	NPD9705	Discontinued
0.6816	Remote Similarity	NPD112	Approved
0.6814	Remote Similarity	NPD4457	Phase 2
0.6811	Remote Similarity	NPD5943	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD2391	Clinical (unspecified phase)
0.6808	Remote Similarity	NPD4995	Approved
0.6808	Remote Similarity	NPD4996	Approved
0.68	Remote Similarity	NPD3932	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6458	Discontinued
0.6798	Remote Similarity	NPD1468	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD3889	Approved
0.6793	Remote Similarity	NPD966	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD6047	Phase 1
0.6789	Remote Similarity	NPD3872	Phase 3
0.6789	Remote Similarity	NPD706	Phase 1
0.6788	Remote Similarity	NPD7722	Suspended
0.6786	Remote Similarity	NPD6468	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD6469	Phase 3
0.678	Remote Similarity	NPD5413	Phase 2
0.678	Remote Similarity	NPD6285	Phase 2
0.6776	Remote Similarity	NPD3960	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD6592	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD3930	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD2128	Phase 1
0.6761	Remote Similarity	NPD4925	Approved
0.6761	Remote Similarity	NPD1900	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD5873	Phase 3
0.6758	Remote Similarity	NPD5874	Phase 3
0.6757	Remote Similarity	NPD7006	Approved
0.6757	Remote Similarity	NPD5065	Approved
0.6755	Remote Similarity	NPD1570	Approved
0.6754	Remote Similarity	NPD3002	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD9695	Approved
0.675	Remote Similarity	NPD5425	Phase 1
0.6749	Remote Similarity	NPD8321	Discontinued
0.6739	Remote Similarity	NPD1567	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD2814	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD4612	Discontinued
0.673	Remote Similarity	NPD4932	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD5804	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD2917	Approved
0.6701	Remote Similarity	NPD3406	Suspended
0.67	Remote Similarity	NPD6545	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD5827	Discontinued
0.6698	Remote Similarity	NPD1572	Phase 2
0.6697	Remote Similarity	NPD6750	Phase 2
0.6685	Remote Similarity	NPD1326	Approved
0.6685	Remote Similarity	NPD1325	Approved
0.6684	Remote Similarity	NPD3504	Approved
0.6684	Remote Similarity	NPD3503	Approved
0.6683	Remote Similarity	NPD6202	Discontinued
0.6683	Remote Similarity	NPD796	Phase 2
0.6682	Remote Similarity	NPD5833	Phase 1
0.6682	Remote Similarity	NPD5045	Phase 2
0.6667	Remote Similarity	NPD4306	Phase 1
0.6667	Remote Similarity	NPD2176	Approved
0.6667	Remote Similarity	NPD7726	Phase 1
0.6667	Remote Similarity	NPD6589	Phase 1
0.6667	Remote Similarity	NPD2177	Approved
0.6667	Remote Similarity	NPD5255	Approved
0.6667	Remote Similarity	NPD5153	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7103	Approved
0.6667	Remote Similarity	NPD6643	Discontinued
0.6667	Remote Similarity	NPD7270	Phase 2
0.6667	Remote Similarity	NPD5828	Phase 2
0.6667	Remote Similarity	NPD2175	Phase 3
0.6652	Remote Similarity	NPD7068	Approved
0.6652	Remote Similarity	NPD7067	Approved
0.6651	Remote Similarity	NPD8004	Discontinued
0.6651	Remote Similarity	NPD3938	Phase 1
0.6651	Remote Similarity	NPD5139	Phase 1
0.6649	Remote Similarity	NPD443	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD5546	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD1571	Phase 2
0.6635	Remote Similarity	NPD4893	Phase 3

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data